Literature DB >> 30820742

Single-stage synthesis of heterocyclic alkaloid-like compounds from (+)-camphoric acid and their antiviral activity.

Vladimir V Chernyshov1,2, Olga I Yarovaya3,4, Dmitry S Fadeev3, Yuriy V Gatilov3,4, Yana L Esaulkova5, Anna S Muryleva5, Katherina O Sinegubova5, Vladimir V Zarubaev5, Nariman F Salakhutdinov3,4.   

Abstract

An effective technique for one-stage synthesis of new polycyclic nitrogen-containing compounds has been developed. The procedure involves refluxing mixtures of camphoric acid with aliphatic or aromatic diamine without catalysts. In cases where the starting amine has a low boiling point (less than 200 °C), phenol is used as a solvent, as it is the most optimal one for obtaining products with good yields. It has been shown that the use of Lewis acids as catalysts reduces the yield of the reaction products. A set of compounds have been synthesized, which can be attributed to synthetic analogues of alkaloids. In vitro screening for activity influenza virus A was carried out for the obtained compounds. The synthesized quinazoline-like agent 14 has inhibitory activity against different strains of influenza viruses.

Entities:  

Keywords:  (+)-Camphoric acid; Alkaloid analogues; Antiviral activity; Antivirals; Influenza virus; Single-stage synthesis

Year:  2019        PMID: 30820742     DOI: 10.1007/s11030-019-09932-9

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


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